Hydrochloric Acid → HCID 70590013, compound

HRID 2052036Notes

Reaction equation

HRID 2052036 reaction equation
[Cl:1]C1C(Cl)=CC=CC=1OC.C(Cl)(=O)CC.[Cl-].[Al+3].[Cl-].[Cl-].Cl.Cl[C:22]1[C:27]([Cl:28])=[C:26]([O:29][CH3:30])[CH:25]=[CH:24][C:23]=1[C:31](=[O:34])[CH2:32][CH3:33]>C(Cl)Cl>[Cl:28][C:27]1([Cl:1])[C:26]([O:29][CH3:30])=[CH:25][CH:24]=[C:23]([C:31](=[O:34])[CH2:32][CH3:33])[CH2:22]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 161262,3-DichloroanisoleHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 20378237HCID 20378237, compound

Product 1

HCID 70590013HCID 70590013, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A stirred mixture of 2,3-dichloroanisole (177.0 g., 1.0 mole) and propionyl chloride (101.8 g., 1.1 mole) in methylene chloride (600 ml.) is cooled to 5° C. and treated with aluminum chloride (146.7 g., 1.1 mole) during a 11/2 hour period. The reaction is allowed to warm to 25° C. and after 16 hours is poured into ice-water (2 l.) and concentrated hydrochloric acid (200 ml.). The organic phase is washed with 10% sodium hydroxide solution and saturated salt solution, and dried over magnesium sulfate. After evaporation of the solvent, the product is crystallized from hexane to give 124.5 g. (53%) of 2',3'-dichloro-4'-methoxypropionphenone which melts at 51°-54° C.

Workup

  1. temperatureto warm to 25° C. and after 16 hours
  2. washThe organic phase is washed with 10% sodium hydroxide solution and saturated salt solution
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe product is crystallized from hexane
  6. customto give 124.5 g

Sources & evidence

ORD record
ord-0c1013d81ea04b0fa65e975eab967566
Source dataset
uspto-grants-1980_01
Patent number
US04182764

Reaction notes

Loading…